St. Simon (1881 – April 2, 1908) was an undefeated British Thoroughbredracehorse and one of the most successful sires in the history of the Thoroughbred. In May 1886 The Sporting Times' carried out a poll of one hundred experts to create a ranking of the best British racehorses of the 19th century. St. Simon was ranked fourth, having been placed in the top ten by 53 of the contributors.[1]

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Foaled at William Barrow's Paddocks near Newmarket, St. Simon was by the good racehorse and sire Galopin. Galopin won 10 out of 11 races, including the Epsom Derby, and was a leading sire three times. His get included the dams of Triple Crown winner Flying Fox and Bayardo. At the time of St. Simon's birth, however, he had not produced his best stock.

St. Simon's dam, St. Angela (by King Tom), was disappointing as a broodmare up to the time she had her sixth foal, St. Simon, at 16. However, she did produce the sisters to St. Simon, Simonne II and Angelica (both by Galopin), dam of the stallion Orme (1889 by Ormonde).[2]

St. Simon was a brown colt with a small star on his forehead and a few white hairs on the inside of his pasterns and heels. He also tended to produce bay or brown foals, with the exception of his final foal, a grey filly. His final height was 16 or 16.1 hands (1.63 or 1.65 m) (sources differ in opinion), but his fine build made him look even smaller. His offspring also were usually slightly smaller than average. He had a fine head that was slightly dished, clean legs—although quite over at the knee—and a short back (another trait his offspring tended to inherit). He also had strong quarters and a very good shoulder, which was called "a study. So obliquely was it placed that it appeared to extend far into his back, making the latter look shorter" by the 1916 Bloodstock Breeders Review. His girth was said to be 78 inches (2.0 m), and his cannon bone 81⁄2 inches (220 mm) around.

The death of his owner in May 1883 led to a dispersal sale of all his stock, where he was purchased for 1,600 guineas by the 25-year-old Duke of Portland, and moved to Mathew Dawson's Heath House stables at Newmarket.

The colt began his racing career under jockey Fred Archer at the five furlong Halnaker Stakes at Goodwood, winning by six lengths, and the following day he won the six-furlong Maiden Plate (for which he was eligible because he was a maiden at the time of his entry) by a length, carrying 9 stone 7 pounds (133 lb). He then easily won a five-furlong race against Clochette and Fleta, the five-furlong Devonshire Nursery Plate (against 19 other horses, carrying 8 stone 12 pounds (124 lb) by two lengths at a canter, and the seven-furlong Princes of Wales's Nursery Plate (Doncaster) carrying 9 stone (130 lb; 57 kg) and winning by eight lengths against 21 other horses. St. Simon followed this by a win in a six furlong match against Duke of Richmond to end his two-year-old year considered the best of his age, despite not winning a major stakes race.

St. Simon was prevented from running in the classics because the death of Prince Batthyany had invalidated his entries. His three-year-old career began with an unofficial trial race at Newmarket in which he was matched against the leading older horse Tristan at weight-for-age over one and a half miles at Newmarket.[3] St Simon won very easily by six lengths. St. Simon then won by a walkover at the 10-furlong Epsom Gold Cup. He then won the 2½ mile Ascot Gold Cup by 20 lengths, despite having trailed in the beginning of the race, to beat Tristan and Faugh-a-Ballagh, and was so strong that it took almost a whole lap for his jockey to pull him up.[2] In the one-mile Newcastle Gold Cup, he beat his only other competitor, Chiselhurst, by eight lengths, but suffered some damage due to the hard ground. He then defeated former St. Leger winner Ossian by 20 lengths in the 2½ mile Goodwood Cup. Additionally, St. Simon had easily beaten The Lambkin (who would win that year's St. Leger) and that year's 2,000 Guineas Stakes winner, Scot Free.

The Newcastle Cup running caught up to him, producing serious leg problems. St. Simon was kept in training in 1885, and there were hopes of a meeting with the other leading colt of his generation St. Gatien.[4] He did not recover, however, and never raced again, beginning his breeding career at the age of five.